diff --git a/handlers/business_updates.py b/handlers/business_updates.py
index c1d4a8e..4a5f8ee 100644
--- a/handlers/business_updates.py
+++ b/handlers/business_updates.py
@@ -207,9 +207,41 @@ def _deliver_auto(conn, message, customer_text: str, reply_text: str) -> None:
             "reply permission. Check Telegram Business → Chatbots."
         )
         return
-    telegram_api.send_reply(handlers.bot, customer_chat_id, reply_text,
-                            business_connection_id=bcid,
-                            reply_to_message_id=message.message_id)
+    try:
+        telegram_api.send_reply(
+            handlers.bot,
+            customer_chat_id,
+            reply_text,
+            business_connection_id=bcid,
+            reply_to_message_id=message.message_id,
+        )
+    except telegram_api.TelegramPartialSendError as exc:
+        log.error(
+            "auto-reply partially delivered chat=%s chunks=%d/%d",
+            utils.mask_id(customer_chat_id),
+            exc.sent_count,
+            exc.total_count,
+        )
+        name = business_service.customer_display_name(bcid, customer_chat_id)
+        handlers.notify_owner(
+            f"⚠️ An automatic reply to <b>{utils.escape(name)}</b> was only "
+            f"partially delivered ({exc.sent_count}/{exc.total_count} parts). "
+            "Check the customer chat before sending anything else."
+        )
+        return
+    except Exception as exc:
+        log.warning(
+            "auto-reply delivery unconfirmed chat=%s error=%s",
+            utils.mask_id(customer_chat_id),
+            type(exc).__name__,
+        )
+        name = business_service.customer_display_name(bcid, customer_chat_id)
+        handlers.notify_owner(
+            f"⚠️ Delivery of an automatic reply to <b>{utils.escape(name)}</b> "
+            "could not be confirmed. No outbound history was recorded; check "
+            "the customer chat before retrying."
+        )
+        return
     database.insert_message(bcid, customer_chat_id, None, "out", "assistant", reply_text)
     memory_service.append_exchange(bcid, customer_chat_id, customer_text, reply_text)
     log.info("auto-replied chat=%s len=%d", utils.mask_id(customer_chat_id), len(reply_text))
diff --git a/tests/unit/handlers/test_business_updates.py b/tests/unit/handlers/test_business_updates.py
index 4e33adb..8f35d0f 100644
--- a/tests/unit/handlers/test_business_updates.py
+++ b/tests/unit/handlers/test_business_updates.py
@@ -162,6 +162,40 @@ def test_deliver_auto_records_outbound(db, stub_bot, make_message, mocker):
     assert _out_count(db) == 1
 
 
+def test_deliver_auto_warns_on_partial_delivery(db, stub_bot, make_message, mocker):
+    mocker.patch(
+        "telegram_api.send_reply",
+        side_effect=bu.telegram_api.TelegramPartialSendError(1, 2),
+    )
+    notify = mocker.patch("handlers.notify_owner")
+    db.upsert_business_connection("bc1", 999, True, True)
+    conn = db.get_business_connection("bc1")
+
+    bu._deliver_auto(conn, make_message(chat_id=5), "ctext", "reply text")
+
+    assert "partially delivered (1/2 parts)" in notify.call_args.args[0]
+    assert _out_count(db) == 0
+    assert db.get_recent_memory("bc1", 5, 10) == []
+
+
+def test_deliver_auto_warns_when_delivery_is_unconfirmed(
+    db, stub_bot, make_message, mocker
+):
+    mocker.patch(
+        "telegram_api.send_reply",
+        side_effect=bu.telegram_api.TelegramAPIError("unavailable"),
+    )
+    notify = mocker.patch("handlers.notify_owner")
+    db.upsert_business_connection("bc1", 999, True, True)
+    conn = db.get_business_connection("bc1")
+
+    bu._deliver_auto(conn, make_message(chat_id=5), "ctext", "reply text")
+
+    assert "could not be confirmed" in notify.call_args.args[0]
+    assert _out_count(db) == 0
+    assert db.get_recent_memory("bc1", 5, 10) == []
+
+
 # --- deleted messages --------------------------------------------------------
 def test_deleted_invalidates_approval(penv):
     aid = penv.db.insert_pending_approval("bc1", 5, 22, "c", "r")